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J Scognamiglio et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50 Suppl 3, S557-S561 (2012-03-27)
A toxicologic and dermatologic review of 3-methyl-2-(pentyloxy)-2-cyclopenten-1-one when used as a fragrance ingredient is presented. 3-Methyl-2-(pentyloxy)-2-cyclopenten-1-one is a member of the fragrance structural group ketones cyclopentanones and cyclopentenones. The common characteristic structural element of the group members is a cyclopentanone
Anke Jakobs et al.
The Journal of biological chemistry, 291(50), 26098-26108 (2016-11-03)
Recent work has demonstrated pro-oncogenic functions of the transcription factor CCAAT box/enhancer-binding protein β (C/EBPβ) in various tumors, implicating C/EBPβ as an interesting target for the development of small-molecule inhibitors. We have previously discovered that the sesquiterpene lactone helenalin acetate
Nanaji Arisetti et al.
Organic letters, 17(1), 94-97 (2014-12-17)
The pseudoenantiomeric 4-O-Boc- and 4-OPMP-cyclopent-2-enones, readily available from hydroxymethylenefurane on multigram scale, are demonstrated to be exceptional building blocks for the synthesis of enantiopure 4-alkyl-5-(1'-hydroxyalkyl) substituted 2-cyclopentenones and derivatives thereof. The 4-OR substituent acts as a traceless stereoinducing element, conferring
Mats Linder et al.
Physical chemistry chemical physics : PCCP, 15(14), 5108-5114 (2013-03-02)
This work discusses the dependence of transition state geometries on the choice of quantum chemical optimization method for the extensively studied Diels-Alder reaction. Rather significant differences are observed between post-Hartree-Fock methods and (hybrid) density functional theory, where the latter predicts
Diverse reactivity in a rhodium(III)-catalyzed oxidative coupling of N-allyl arenesulfonamides with alkynes.
Dongqi Wang et al.
Angewandte Chemie (International ed. in English), 51(49), 12348-12352 (2012-10-31)
Sean W Harshman et al.
Journal of breath research, 9(4), 047103-047103 (2015-10-28)
Pilots have reported experiencing in-flight hypoxic-like symptoms since the inception of high-altitude aviation. As a result, the need to monitor pilots, in-flight, for the onset of hypoxic conditions is of great interest to the aviation community. We propose that exhaled
Henrik U Stotz et al.
Journal of experimental botany, 64(4), 963-975 (2013-01-26)
Jasmonates and phytoprostanes are oxylipins that regulate stress responses and diverse physiological and developmental processes. 12-Oxo-phytodienoic acid (OPDA) and phytoprostanes are structurally related electrophilic cyclopentenones, which activate similar gene expression profiles that are for the most part different from the
Brad M Loertscher et al.
Organic letters, 15(8), 1930-1933 (2013-04-12)
A strategy for the synthesis of differentiated vicinal tertiary diols is described. The key step is a high-yielding, diastereoselective LaCl3·2LiCl-mediated addition of a Grignard or organolithium reagent to ketone 2a. The reaction is believed to proceed via a 1,3-chelated intermediate.
Jana Fišanová et al.
Journal of molecular modeling, 18(10), 4751-4759 (2012-06-14)
Geometries, vibrational frequencies, vertical and adiabatic excitation energies, dipole moments and dipole polarizabilities of the ground and the three lowest electronic excited states, S₁(n, π*), T₁(n, π*), and T₂(π, π*) of the 2-cyclopenten-1-one molecule (2CP) were calculated at the CCSD
Sadiya Raja et al.
Chemistry, an Asian journal, 7(10), 2361-2366 (2012-08-02)
A Brønsted acid-catalyzed asymmetric Nazarov cyclization of acyclic α-alkoxy dienones has been developed. The reaction offers access to chiral cyclopentenones in a highly enantioselective manner. The reaction is complementary to our previously reported Brønsted acid-catalyzed electrocyclization reactions, which provided differently
Brett D Schwartz et al.
Organic letters, 15(8), 1934-1937 (2013-04-05)
The title natural product, 1, has been synthesized in 20 steps from the enantiomerically pure cis-1,2-dihydrocatechol 2, itself obtained through the whole-cell biotransformation of toluene. The pivotal steps in the reaction sequence involve a Diels-Alder cycloaddition reaction between diene 2
Yanan Zhai et al.
Fungal genetics and biology : FG & B, 129, 7-15 (2019-04-14)
Eupenifeldin, a bistropolone meroterpenoid, was first discovered as an antitumor agent from the fungus Eupenicillium brefeldianum. We also isolated this compound and a new congener from a strain of Phoma sp. (CGMCC 10481), and evaluated their antitumor effects. Eupenifeldin showed
Gergely Morten Solecki et al.
Chemical research in toxicology, 26(2), 252-261 (2013-01-24)
Prostaglandins are endogenous mediators formed from arachidonic acid by cyclooxygenases and prostaglandin synthases during inflammatory processes. The five-membered ring can be dehydrated, and α,β-unsaturated cyclopentenone PGs (cyPGs) are generated. Recent studies have been focused on their potential pharmacological use against
Xiaoxun Li et al.
Organic letters, 14(6), 1584-1587 (2012-03-03)
Functionalized cyclopentenones were synthesized by a Rh-catalyzed carbonylation of 3-acyloxy-1,4-enynes, derived from alkynes and α,β-unsaturated aldehydes. The reaction involved a Saucy-Marbet 1,3-acyloxy migration of propargyl esters and a [4 + 1] cycloaddition of the resulting acyloxy substituted vinylallene with CO.
Yoichi Noya et al.
Toxicology, 314(1), 1-10 (2013-08-29)
Smoking is a major risk factor for atherosclerotic vascular diseases, but the mechanism for its genesis is unknown. We have recently shown that the gas phase of cigarette smoke (nicotine- and tar-free cigarette smoke extract; CSE) likely to reach the
Daniel J Kerr et al.
Organic letters, 14(7), 1732-1735 (2012-03-30)
Oxazolidinones are powerful promoters of the Nazarov reaction, enabling the cyclization of conventionally resistant substrates to be achieved under mild conditions. They exert excellent regio- and torquoselective control in both the conventional Nazarov reaction giving cyclopentenones and in the "interrupted"
Wei Chen et al.
The Journal of organic chemistry, 77(14), 6215-6222 (2012-06-26)
A class of alkenyl propargyl acetates, RCH(OAc)C≡CC(CH(3))═CH(2) (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that
Nolan K Maier et al.
Journal of immunology (Baltimore, Md. : 1950), 194(6), 2776-2785 (2015-02-15)
Inflammasomes are cytosolic protein complexes that respond to diverse danger signals by activating caspase-1. The sensor components of the inflammasome, often proteins of the nucleotide-binding oligomerization domain-like receptor (NLR) family, detect stress, danger stimuli, and pathogen-associated molecular patterns. We report
Valerii Z Shirinian et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 12(9), 1717-1725 (2013-06-28)
A wide range of new oxime-based photochromic diarylethenes of the cyclopentenone series have been synthesized. Their spectral properties have been investigated in detail upon UV/vis light irradiation in acetonitrile solution, and distinct correlations between photochromic characteristics and substance structures are
Rachel Lerebours et al.
Organic letters, 9(14), 2737-2740 (2007-06-15)
Palladium-phosphinous acids catalyze the conjugate addition of arylsiloxanes to a wide range of alpha,beta-unsaturated substrates in water. A microwave-assisted procedure is described that uses 5 mol % of POPd1 to afford beta-substituted ketones, aldehydes, esters, nitriles, and nitroalkanes in 83%
Bangyu Liu et al.
Chemical communications (Cambridge, England), 49(22), 2201-2203 (2013-02-12)
Palladium-catalyzed cyclization of β-alkylthio dienone derivatives affords 2-cyclopentenones in a regio- and stereoselective manner in the presence of silane. C-S activation, intramolecular carbopalladation and hydrogenolysis construct the cascade process.
Masaharu Sugiura et al.
Organic letters, 16(19), 5172-5175 (2014-09-24)
Enantioselective conjugate addition of styrylboronic acid to dienones was effectively catalyzed by an O-monoacyltartaric acid to afford monostyrylated products with good enantioselectivity. The RCM of the monostyrylated products using the Hoveyda-Grubbs II catalyst afforded optically active cyclopentenones, including a synthetic
Shailaja Hegde et al.
Blood, 118(26), 6909-6919 (2011-10-05)
Targeting cancer stem cells is of paramount importance in successfully preventing cancer relapse. Recently, in silico screening of public gene-expression datasets identified cyclooxygenase-derived cyclopentenone prostaglandins (CyPGs) as likely agents to target malignant stem cells. We show here that Δ(12)-PGJ(3), a
Haiyan Shi et al.
Marine drugs, 10(6), 1331-1344 (2012-07-24)
Nine new compounds, namely sinularones A-I (1-9), characterized as cyclopentenone and butenolide-type analogues, were isolated from a soft coral Sinularia sp., together with a known butenolide (10). Their structures were elucidated by means of spectroscopic (IR, MS, 1D and 2D
Sebastian Lungu-Mitea et al.
Scientific reports, 8(1), 12380-12380 (2018-08-19)
The nuclear factor erythroid 2-related factor 2 (Nrf2) is a key regulator of cellular defense against oxidative stress and correlated with classical toxicological endpoints. In vitro methods using fish cell lines for the assessment of aquatic toxicity are needed for
Aldrichimica Acta, 19, 42-42 (1986)
Yoshihiro Sumiyoshi et al.
The Journal of chemical physics, 125(12), 124307-124307 (2006-10-04)
Pure rotational transitions in the ground state for Ar-OH and Ar-OD [Y. Ohshima et al., J. Chem. Phys. 95, 7001 (1991) and Y. Endo et al., Faraday Discuss. 97, 341 (1994)], those in the excited states of the OH vibration
Sereyvath Yoeun et al.
BMB reports, 46(3), 151-156 (2013-03-27)
Phylogenetic and amino acid sequence analysis indicated that rice allene oxide synthase-1 (OsAOS1) is CYP74, and is clearly distinct from CYP74B, C and D subfamilies. Regio- and stereo-chemical analysis revealed the dual substrate specificity of OsAOS1 for (cis,trans)-configurational isomers of
Agustí Lledó et al.
Chemical communications (Cambridge, England), 49(29), 3055-3057 (2013-03-07)
Medium sized trans-cycloalkenes are unusually reactive in the intermolecular Pauson-Khand reaction (PKR) with regard to typical monocyclic alkenes. This is due to the ring strain imparted by the E stereochemistry. The PKR of these alkenes offers a modular, regioselective and
Jesse R Poganik et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 33(12), 14636-14652 (2019-11-02)
The nuclear factor erythroid 2-related factor 2 (Nrf2) signaling axis is a target of covalent drugs and bioactive native electrophiles. However, much of our understanding of Nrf2 regulation has been focused at the protein level. Here we report a post-transcriptional
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